Finding the Operational Pain Behind “We Already Have This”

1. You’ve moved through nearly every stage of Chekin’s commercial structure in two years — from customer service, to Account Executive covering mid-market Spain, to Strategic Account Executive, and now Enterprise BDM. What changed most in how you sell once the conversation shifted from a single mid-market operator to a hotel chain managing compliance across dozens of properties?

The biggest change is that you stop selling a feature and start selling a solution to a much bigger operational problem.

With a mid-market operator, the conversation can be quite straightforward. You might be talking to the person who actually manages the day-to-day operation, so they know exactly where the pain is and they can make decisions relatively quickly.

With a hotel chain or a large enterprise group, it’s completely different. You have multiple properties, different teams, sometimes different PMSs, different regulations depending on the country, and several stakeholders involved in the decision.

So my role became much more about understanding how everything fits together before even talking about Chekin. Who owns compliance? What is still manual? How does information move between the PMS, the guest and the property? What happens when they open another 20 properties?

I think that was the biggest change for me: I stopped thinking so much about “how do I sell Chekin?” and started thinking more about “how would Chekin actually fit into this company and scale with them?”

2. Chekin’s compliance coverage now spans 45+ countries, and regulations like tourist tax reporting and police registration keep shifting country by country. When you’re prospecting enterprise operators, is regulatory pressure something you have to explain to them, or are they already coming to you because they’ve been burned by it?

It’s actually a mix of both, but with larger operators they normally already understand the problem.

You rarely need to convince a hotel group that compliance matters. What you often discover, though, is that they don’t realise how fragmented their current process has become.

They might have one process in Spain, another in Italy, something completely different in Portugal, and then a lot of manual work happening at property level to make everything work.

And yes, sometimes you speak with companies that have already had problems — failed police submissions, changes in regulation, staff manually correcting registrations, or simply spending hours every week doing something that shouldn’t require that much human involvement.

That’s when the conversation becomes interesting, because compliance is the reason you enter the conversation, but operational efficiency is normally where the real value becomes obvious.

3. You describe your job as helping teams who “don’t wake up excited about guest registration, ID verification, or compliance.” For an enterprise buyer evaluating Chekin against a dozen other automation vendors, what’s the one objection you hear most often, and how do you actually get past it?

One of the most common objections is basically: “We already have something that does this.”

And most of the time, they’re right. Enterprise companies usually already have a PMS, payment provider, guest communication tool, access system, maybe an internal solution, and sometimes several different tools doing parts of what Chekin does.

So I don’t try to convince them that everything they have is wrong. I actually want to understand what happens between those systems.

Where does someone still have to manually check something? Where does the guest experience break? What happens when a payment fails? Who checks whether registration was completed? How are access codes released? What happens when you add another property or another country?

Usually, that’s where you find the real problem.

For me, the goal isn’t to win an argument about features. It’s to find out whether there’s enough operational pain for changing the current process to actually make sense. And sometimes there isn’t  and I think being comfortable saying that also builds a lot of trust with enterprise buyers.

4. Before hospitality tech, you worked behind a bar in Dundee and did market research for a meal-kit business in Tenerife. Does anything from those very different jobs still show up in how you run outbound today?

Definitely. Probably more than I expected.

Working behind a bar teaches you very quickly how to read people. You speak with hundreds of completely different personalities, and you learn that you can’t communicate with everyone in exactly the same way. I think that translates directly into sales.

The market research role was different, but it taught me to ask questions without assuming I already knew the answer. That’s something I use constantly in outbound and discovery today.

And hospitality itself helped a lot too. If you’ve worked in it, you understand that people at property level are busy. They don’t want another piece of software just because it has 20 features. They want something that removes work from their day.

So even though bartending, market research and enterprise SaaS sales look completely unrelated on paper, I think all three taught me the same thing: listen first, understand what the person in front of you actually needs, and then adapt the conversation from there.